My daughter lives in Kailua on Oahu and although I know you have no plans to go to Oahu, it's a super nice area. Just be aware that Hawaii just passed an extremely stringent law concerning vacation rentals and what's available now may not be rentals one year from now.

Everyone's different. I have to have a pool when I'm doing a tropical vacation myself. It's one of my favorite things. And personally I wouldn't want to change places and stay on two islands in four different hotels with only a two week trip myself. Plus if you are trying to rent a home thru private channels often there are one-week minimums to consider.

why is everything posting in italics here????

Interesting....Do owners have to be licensed or something? I have been looking via VRBO and hoping to rent that way.

Yes, they will have to be licensed, and there will be a limit on the number of licensed vacation rentals.

Legitimate vrbo rentals will include their tax id.

You need to check the short term rental regulations for each county as they're different. This information can usually be found on each county's website. The recent laws passed by Honolulu County apply to the island of Oahu which you don't appear to be going to.

On Kauai, legal rentals will provide their license ID which is called a TVR, and NOT the same as a tax id. If you rent an illegal unit and it gets shut down, you would have to scramble to find an alternate lodging and may well pay sky high prices. Also look into renting a condo from an on island agency such as Parrish, Suite Paradise and others. If the unit is unsatisfactory, it would be easier for an agency to find you an alternate unit vs an individual owner on VRBO.

VRBO guarantees your lodging satisfaction (they will boot owners for not providing what they say they will, and even keep track of owners who cancel reservations too many times, and will kick them off). Vrbo even deals with deposit and damage deposit refunds on an automatic basis now, instead of letting owners hold funds. It's a much tighter ship since they started taking a piece of the acton instead of being just a site for 3rd part rentals.
if you have questions or concerns, their reps will answer them.

Each island is unique and offers a slightly different experience for the same activity. Hiking on Maui is pretty spectacular due to Haleakala National Park whereas Kauai will be mostly rainforest and waterfalls. You can get a lot of that on Maui too. Kauai is for those who really want to get away and relax yet not so isolated as the islands of Molokai or Lanai.

I was on the beach today here on Maui and yes there are some crazy busy spots but if you are using a vacation rental that is out of the way then there are plenty of quiet places your host will direct you to.

Heading over to the Big Island is always fun. I would only put a couple of days in Hilo and put the rest of my time in the Kona area, exploring some of the historical sites and doing unique activities like Manta Ray or star gazing.

Thank you everyone for the information on destinations and rentals. We are getting closer to booking The Big Island (possibly 2 nights near Hilo, 5 nights near Kona) and 1 full week on south shore of Maui...Kauai will have to wait for another trip! I'm just waiting on the ability to book airfare for that period and then will move to booking lodging/car /etc. Appreciate your ideas and help!

<Kauai will be mostly rainforest and waterfalls>

Kauai has those, but SO much more. Don't forget Waimea Canyon, the Grand Canyon of the Pacific, and the adjacent Koke'e State Park. It is spectacular -- and there's nothing like that on any other island.

I am not a big fan of Maui. It's just too crowded and overdeveloped for my taste. But I do love Haleakala and some of the areas near Hana.

Kauai is pretty spectacular. Return visitors to Hawaii should definitely have it on their list. I think first-time visitors to Hawaii underappreciate the island and desire a bit more town/city action than what Kauai can provide. Visitors want to get away from the "city" but still want the "town" services on their vacations (restaurant & shopping options, shows, some-what populated beaches - empty beaches make people nervous).

I’m not trying to sell anyone on Kauai. All the islands have their pros and cons. But I think there are some misconceptions about how “undeveloped” Kauai is. We have Costco, Walmart, at least a half dozen supermarkets, four luaus, a shopping mall with Macy’s, a Home Depot, and a multiplex movie theater. Lots of golf courses and putt-putt golf. The big hotels all have nightly entertainment, as do quite a few bars.



There are enough upscale, excellent restaurants for a typical vacationer to enjoy an awesome meal at a different restaurant every night of their vacation. Of course, Kauai doesn’t have the variety of nightlife and restaurants you’ll find on Oahu and Maui. But it has more than enough.



You would have to hike treacherous trails to even have a chance of finding an empty beach. Ke’e Beach (which is incredibly beautiful) recently instituted reservation-only parking limited to 900 vehicles a day. I wouldn’t call the beach at Hanalei Bay “crowded,” but on a nice day, there are hundreds of people spread out. The big difference is that there are almost no condos or hotels visible from the beaches, and while there are lots of sunbathers, there is a lot of room, so you are never on top of the next people.



My niece and her husband went to Maui every year and loved it. They thought they would hate Kauai. But once they tried it, they never returned to Maui. But again, everyone has different tastes—and I like all the islands for different reasons. But I don’t come to Hawaii to feel like I’m in a city—and Kauai (specifically the North Shore) is the only place that feels like my fantasy of “Hawaii” – the tropical paradise.



Kalalau Lookout, Koke'e State Park



Hanalei Bay




Waimea Canyon